Water → 2-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetic acid

HRID 453501Notes

Reaction equation

HRID 453501 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:29]=[CH:28][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25]C)=[O:24])=[CH:18][C:17]=3[Cl:27])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].O>C1COCC1.C(Cl)Cl.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][C:17]=3[Cl:27])=[CH:28][CH:29]=2)=[O:10])=[CH:30][CH:31]=1

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 68466220Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetate

Product 1

HCID 594031892-(4-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetic acidYield 59.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-chlorophenyl)acetate (33 mg, 0.0720 mmol) was diluted with THF (500 μL) followed by the addition NaOH (0.144 ml, 0.720 mmol) and 100 μL of water. After stirring for 2 hours, the reaction was diluted with DCM and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 2-(4-(4-((4-chlorophenethyl) carbamoyl)phenoxy)-3-chlorophenyl)acetic acid (19 mg, 59.4% yield) as a white solid. 1H NMR (400 MHz, CDCl3/CD3OD) δ 7.65 (d, 2H), 7.42 (m, 1H), 7.25 (d, 2H), 7.20 (d, 1H), 7.15 (d, 2H), 7.05 (d, 1H), 6.85 (d, 2H), 3.65 (t, 2H), 3.60 (s, 2H), 2.90 (t, 2H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cac843f0577544f19955be11a4ddcab2
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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